The COO Survival Guide: How to Nail the Hardest Parts of Leading Ops

Sean Mowdri, COO at ZenPilot, talks through the hardest parts of running operations: decision-making, which metrics actually matter, and how to stay productive using tools like ClickUp. Practical advice for ops leaders at smaller agencies.
Hello, hello, hello everyone, and welcome to the Zen Pilot live show. It's been a while since I got a chance to say that. Hello, everyone. Welcome to the show today. And my guest on the call is Sean Mowdri, COO at Zenpilot, our CEO Sean, how are you doing today?
I am great. I'm so excited to be here with you and looking forward to seeing who joins us today.
Yes, I'm looking forward to seeing that too. Watchers and listeners, hello. And if you're watching the recording, we greet you all the same. But if you're watching live, definitely let us know in the comments so you can see us and you can hear us. I've got slides today. Let me show them to you. So here's our welcome slide. And just in case you need to run in just a second, I encourage you to sign up to the ZenPilot newsletter so you can get informed in advance about our live streams and webinars and other events and other content so you can make more concrete plans and block off your calendar. Nobody disturbed me. Zenpilot is streaming. So, yeah, definitely let us know that you can see us and hear us. I'll be highlighting the comments as we go. And one little fun thing that I thought we might start with is we've got you, Sean, on the call here today with a ton of ops experience and definitely won't be able to learn everything you know in just this one little hour that we've got here. But you as the audience, watchers and listeners can steer the conversation. Have a look at this list that we've got for you here and tell us what you would like to learn most about today. Give us a number. We've got one to nine technically. So these are all the things that we could touch upon today. So leave a number in the comments and let us know what you would like to know about the most. I'll leave that on the screen so you can decide. You can pick more than one number, but just let us know about what you've got. Okay, I've got a comment coming in from Adam. Hi, Adam. After 15 hours of YouTube and three Harry Potter books worth of blogs, I'm excited to finally be able to be on Live. Wow, zenpilot fan. Thank you so much. Emily's with us too. Hi, Emily. Okay, Sean, a quick question to you. As the watchers and listeners pick what they would like to hear most about from your perspective, who do you hope will be tuning in today? Who do you think will benefit the most from listening to a conversation like this.
Yeah. Well, I'm grateful for anybody that's tuning in and listening. I appreciate that. But I think ideally, if you are leading two or more individuals or two or more departments or aspire to be, this is for you.
Yeah, yeah, that's perfect. And I can see that some people are already indicating what they would like to hear about. We've got some interest in how to make good decisions as coo, what metrics to measure tools. I'll be very interested to hear more about that. And EOS succeeding as an integrator. I was curious about that. So we'll see where that takes us. Okay. Leave that on the side on the screen for just a moment longer in case anybody else wants to let us know what you would like to hear about. In the meantime, Sean, I would like to ask you the traditional question I always ask on the podcast, always ask you on the live stream. What is your number one tip for agency operators? I haven't had a chance to ask you yet.
Yeah, well, approximately half of my operating experience or operator experience is in the agency space. So I think the number one tip I would say, and this really applies to any industry, is to find a system to keep yourself and your company, if possible your company, find a system to keep yourself organized. You want to create efficiencies, and then ideally, the reason I say that is because you want to allow time to be present and engaged with your team. The more integrated you are with a team, I think the better the results that you have. So if you have a system to keep you organized, that will allow you to spend more time with the team.
Okay, so in terms of a system to keep organized, is there a particular system that you use or. If I'm thinking I want to build a system like that for myself, where do I start?
Yeah, exactly. Well, I've been around a while, so I've tried many, from notebooks to files to drives to all sorts of tools. But thinking specifically of the agency space, my favorite, that of course tries transparently, we are using right here as an organization is ClickUp. The reason I love it is because we, and you can attest to this, but we as an organization, everything, nearly everything in our organization is in ClickUp. And so I don't have to spend my time or my day poking around digging for data, digging for results. It's just all in one place. I can see where everything is. I know what everybody's working on, and then I can free my time up to actually do the real work or ask the important questions. And Spend the time with the team. That's been my favorite.
Yeah, ClickUp is huge and can be very helpful. I've seen it develop over the years. If some of you watchers and listeners haven't given it a try yet, now is an excellent time to give it a try. And it's just been growing. I remember being excited a year and change ago about, for example, Universal search within ClickUp where you don't have to leave ClickUp to search through your Dropbox. Search through your Google Drive that is already here. They were just announcing ClickUp chat as well and they're promoting it now too, where you can click keep your chat in ClickUp as well. And they just keep growing and growing to make things more integrated.
Absolutely. I have used other tools similar to it. I've just found that it's the most robust, can be dangerous, but it's definitely the most robust tool that everything can go in one spot. I've loved it.
Exactly. Yeah. Keep organized. I like that tip. I think we can dig more into this as we go on. Some more input from our watches and listeners on what they want to hear about. I'll keep that in mind. And yes, Adam, Universal search is awesome. Give it a try. It's really, really cool. Alrighty, so let's move on through the presentation before we move on to answering the questions. Quick housekeeping. There are some questions that always pop up. Are you allowed to ask questions during this live stream? Yes, and in fact, you are encouraged. You're joining live. You've got the advantage of being able to ask your questions. I can't guarantee we'll get them all answered, but we'll try. So don't be shy in the chat. And then as for the recording, this is a live stream. We're coming to you live on LinkedIn and on YouTube. Somebody's watching on YouTube. You should let me know because I'm seeing LinkedIn comments, but not YouTube comments yet. So leave one so we'll know it's working. But anyway, the recording both on LinkedIn and on YouTube will be available under the same link, so you don't have to worry about that. You can send this same link to all of your friends and they'll see the recording if we're not live anymore. But if you send it now, they could join us live, which would be super fun. And finally, for more content like this, don't forget to follow us on LinkedIn. Follow us on YouTube and as I mentioned before, to subscribe to our newsletter. You'll get emails in advance about all of our events. And then finally, if, okay, there's somebody watching on YouTube leaving a comment. Thank you so much. Okay. All right. Awesome, awesome. Finally, if somebody's meeting Zenpilot for the first time. Hi. We're not mentioning ClickUp without reason. We're actually the number one solutions partner for ClickUp and we help agencies and other businesses build a more productive, profitable and healthy team by streamlining their operations in ClickUp. We've been in this game since 2018 and what we do in a nutshell is training, coaching, and we also do implementation of the best ClickUp architecture we found for service based businesses. And we are one of the teams that has the most experience of that with that in this space we've served over 3,000 teams. And one thing that I always like to underline is this little line here. This is not just about technical expertise within ClickUp, but we also do the sometimes a little bit difficult work of hand holding pep talks, change management, just helping you make the change really stick so you don't have to change your project management tool again. Alrighty. So with that in mind, let's see about the topics that our audience would like to know here. Today. I pulled up that slide again. Keep picking what you would like to hear about. I'm going to pull it down in just a few minutes so we can focus on the conversation. But for now, where to begin? I am curious about number one, because that is the kind of the angle that I wanted to pick for this particular live stream. Also, out of my own curiosity, I am a little bit ignorant about the COO role in general. So Sean, I would like to ask you first, what in your opinion is the hardest part or the hardest parts of this COO role? What would you say?
Yeah, part of this is going to depend on the organization size that you're in. So if you're in an organization that has multiple CIS suite executives, this, you, you might have a little bit more narrow focus. But I'm going to just make the assumption that there's maybe more people on this, this live that are at medium to small organizations that have like a COO and a CEO. And so your forecast, your focus is a little bit more, more broad. But I think, you know, your mission is to kind of move that company towards its vision and goals and so recognizing that if you make a change to one team or one individual, it's going to have an effect on the other teams and individuals. It's like a lever and pulley system. And so if you, you need to get the lever right for every single team in order to get that, that team or the organization moving towards the goal all at the same time. That's the most challenging for me.
Okay, and do you have any advice on, I mean, I can certainly see how it can be a tough balancing act. So do you have a good advice on how to actually keep things, you know, balanced and influence that system in an ultimately positive way?
Yeah, Abs, absolutely. I think, you know, here's one example. So let's say your company is struggling with revenue and so you could easily just pull one lever. You can pull that sales lever and infuse some cash into your organization. But recognizing that that might be a short sighted solution because it will have an effect on maybe your employer turnover or client churn if you don't have all of the departments aligned or all of your teams aligned. And so, you know, making sure that you're making moves all at the same time. So I think the way you succeed at it, and this is going to sound a little aspirational, but truly have a crystal clear company vision, core value and focus. And if you make sure that the entire team understands that and is bought into it, which is another challenge that really is helpful I think, if you make sure you've got the right people in the right seat. So hiring the right people and then truly if you can prioritize what will move the company forward either the quickest or sometimes if you make one decision, it will have a positive effect on, you know, other issues or teams in the company. So making sure you can prioritize that and then, you know, bonus if you could just try and keep it simple and eliminate the chaos. That's where I usually start.
So I'll start by saying there's a really cool agency journey episode with our CEO Gray. If you're curious about like communicating vision with clarity, just search for agency journey. Clarity is kindness and you'll find the episode where he digs into that. But I also wanted to ask you, Sean, you mentioned part of the solution here is to communicate vision with clarity. I feel like a lot of teams are in a place where they have the vision written out. It's in a doc somewhere. In our case, it's in the ClickUp doc. Right. But they're not. It's like not living. Document might not be the best expression here, but it's just not integrated into the day to day life of the team. Do you have advice on like specific things to do to surface that vision more often?
You're absolutely right. And this is why I mentioned that this, what I previously said sounds a little aspirational. So let me give you something tangible and this, this is probably not going to be the most popular thing statement that I say, but it is not the employee's job to buy into a company's vision. It's the CEO's job to share the vision in a way that resonates with the team. The employees, rightfully so, are all there for their own benefit and hopefully they enjoy their work. So where the COO comes in is to make sure, number one, let's make really good hiring decisions. Hire the best, the smartest, the brightest people that you can for those roles. Make sure that they align with your core values. And then like I said before, if you free yourself up to spend time and engage with the team, you then can actually make some steps forward to move that team in the right direction.
Okay. Okay, I like that. So I'm trying to keep in mind everything that the watchers and listeners are curious about here and let's see if we can move through the points that got surfaced. Another one. And here I wanted to pull up. Just give me a second. So before this live stream, I took some of this to Reddit actually and asked on a few subreddits for input on what people would like to hear about. And there was this one. I just need to find it. About decision making, particularly how you would make a decision. The question I want to ask is basically what's your decision making process? And particularly when you're asked to make a decision that's fairly high stakes in a limited amount of time, what goes through your head to make the best possible decision kind of in the moment or what questions do you ask to arrive at a good decision?
Yeah, absolutely. So, you know, it starts with the vision and that strategic plan. And so if you know what the goal is for the, you know, your 1, 3, 5, 10 year goal, whatever that vision is, hopefully you've taken the time then to break that down and so you have a clear focus on what you're working for each quarter, each month. Then data and analysis becomes one of the key tools that I will work with. So data is going to tell you a story and so you're going to look for two things. You're going to look at where's our pain points and then where are we succeeding and what is the number one thing I can do right now to pivot to have the biggest impact on the company, knowing that you're always going to lead with the greater good in Mind, I think that's, that's, I don't know if that's something that you can teach or if that's just something that you have. But I think if you always keep that in mind because sometimes you're going to have to make really tough choices, but know that you're doing it for the, the betterment of the organization. I think that is where I start with decision making. Secondly, I truly try and listen to the team and the clients because the team is going to, they're, they're going to be passionate about their area of focus. Right. And so if you listen to them, they will tell you what are our clients saying, what are their pain points. You do have to be able to decipher as the coo, what's fact and what's emotion. And of course teaching your team how to come present issues and potential solutions, that's a whole different conversation for a different day. But I think if you can lean into your team and then I use my gut instinct and intuition and so I give everybody permission to just trust your gut because as much as data will tell us a story, there are going to be outliers and there's room for some gray area. And so trusting that gut, I think is, is also really helpful.
I really like the last element you're mentioning here. I feel like it's an unlock in the sense of the decisions should be data informed. But at the end of the day you need to kind of develop a feel for, for the game, so to speak, in this case, the game of business and leadership. And at the end of the day, if you have a strong gut that steers you in the right direction, I can see how these can be combined. I have a couple of follow ups for that. So you're talking about data and using that to inform decisions. One element that watches and listeners and yours truly are curious about is the metrics that you measure. Obviously there's so many ways, so many different ways to slice that pie. Do you have any particular ones that to you are the most important, you follow the most, you pay attention to the most?
Yeah, again, this is going to depend on your specific role, how narrow or broad your role is. But I in particular want to know, I want to know leading and lagging indicators. So if I'm looking at, and, and I'll be honest, one of the key ones I look at is profit and revenue because that's, that's how we, you know, grow as a company and that's how we can have all of the things we want to have as an organization. So I start there for the most part, but then I break it down because maybe it's, maybe I look at that pain point and maybe it's revenue, for example. Well, it would be easy to just look at your sales team, but that's not the reality really. I want to look at, I want to look at where are leads really top of funnel all the way down to the bottom of the funnel. So where are leads coming from? From which ones are converting the most. Then once our clients stay or are in what is their long time or their lifetime value, I want to know the ROI that we're getting on everything. How productive are we as a team? Then I want to see are we looking at Churn? So is there a satisfaction issue that we have? And, and then of course to the end the revenue and profit. So those are some of the high level things I'm looking at.
Okay, so I'm familiar with like part of this story. Definitely. As a marketer, you know, I understand the funnel, I understand Churn leads gen. Definitely. I am curious about the metrics more on the ops side of things. So you mentioned, for example, you know, how productive we are. Can you tell me more about specifically that side of the business? How does it get turned into numbers?
Yeah, exactly. So if you're looking at it more from a people standpoint, I do want to know, do we have a team? So the nice thing about ClickUp again is that we can see how productive everyone is. And I mean that more from a. Are we overburdening our team and we need to hire more? So I can use it for a hiring decision because I can see, see they're just over capacity in their workload or are they under capacity and we can shift workloads around. So that's one area of ops that you might look at to see use it for hiring needs. I might look at accounts receivable. And so are we. Is our, the amount of time that we're taking to collect money from our clients, is there a way we could shrink that down and infuse cash flow into the company? I might look at that. If we are in a really good growth, you know, sprint and we're hiring a lot of team, I want to, I might want to know, you know, how many candidates are coming in, how many are we having final interviews with depending on, you know, what cycle we're in with hiring the individuals. So those would be some more op specific or people specific measurables I'd look at.
You actually mentioned Something very interesting in the sense of, you know, I look at a lot of teams, they have very good data on the sales and marketing side. They've got HubSpot, they've got the CRM and they're really being, you know, the sales and marketing teams are really being motivated to keep track of the activity. You know, something moves through the pipeline market as soon as, as soon as it happens. And then I think there's a smaller proportion of teams that applies the same kind of standard to their internal work. There's almost like a second funnel of tasks being created, the tasks being in progress, tasks being completed. Is it on time, not on time. And definitely ClickUp and its analytics helps with that. The kind of reporting and dashboards we can have there are really important, but you still have to actually do the work. As in HubSpot you have to mark your, your deals, mark the activity. So in ClickUp you also need to mark your tasks properly. That just popped in my head as you were, as you were mentioning that it really.
And we, we look at all of that too that are, are we getting our tasks done on time? Are we getting, you know, we call them rocks. What would be more of a up to a 90 day project rather than a one week task? How, how much progress are we making on those and is there some success stories in there or are there some learnings that we can take from it and some adjustments that need to be made in the next quarter?
Yeah, that's something I didn't see at previous, at my previous company, for example, or maybe it wasn't tracked that way, but with eos and it doesn't have to be eos, but it's really useful that we have this on track, off track dichotomy of quarterly goals. And that's one metric that we pay attention to. Even I know that from my perspective of what's the percentage per department of quarterly rocks that are on track or off track. So I would definitely include that on the list. Monitoring the comments here, there was one, right? There's one question, there's one comment here from Adam that's actually prompting something in my mind as well. What about you're talking about leading and lagging indicators and we will move past metrics at some point in the conversation, but still curious about this one thing. You're talking about leading and lagging indicators. How far back do you look at the leading indicators? I hope I'm using the right term here in the sense of okay, we're looking at leads being generated, but how much value do you tie to like activity metrics? How many calls are being made, how many emails are being sent, how much content is being produced in your mind? Is it, is it easy to get lost in metrics like this? Do you pay much attention to them? What's your take on them?
Well, I think so. I think if metrics are prohibiting you from getting work done, it's a problem. If you're so lost, if you have too many metrics and you're so lost in it that you're spending too much time and not taking action, that's when it becomes a problem. I think it also depends on your organizational structure. So for example, in our organization, and you can attest to this, you have some nitty gritty stats that you're measuring every single day. Then many of you that have heard from Jeff, he might be looking at some higher level growth statistics and then when I'm looking at it, I'm looking at even higher level statistics. So you might be looking at your daily activity, Jeff might be looking at some leading and lagging. And then I'm going to be looking a little bit more at the lagging indicators. Again, it's going to depend on your company's structure. But I know if, for example, we're not closing enough revenue, the, the revenue number isn't the issue. I need to go back a couple steps and find out where there's maybe a gap that we need to address.
Right. Yeah. And then, you know, if you talk with Jeff about his metrics, he can then talk to me about, for example, the amount of content being published. Everybody owns their own numbers in that sense.
Exactly. Well, and if, again, if you're making, if you are hiring great people in your teams that you can trust and you know that they, they know how important measurables are, then you can trust they're looking at their portion of the metrics, if you will. So everybody's looking at it from every angle so it doesn't fall through the cracks.
All right, thank you for that. Let me check the comments real quick here. Adam, I am seeing your question, but I'm not sure I'm understanding it. Sorry about that. I'll move on for now, try to maybe rephrase it and we'll get back to it later. Touching upon one thing you said earlier, Sean, you mentioned when you listen to the team, when you ask them questions, there's the issue of separating fact from, from emotion. And I think this is one of the toughest parts of being a leader personally, having had that experience at Some point, I was leading a team of 10 and you want to know what's fact and what's emotion. There's a point where you need to push back a little bit against the message and the story that you're getting from your team. And I wanted to get your advice on this. Do you have particular phrases, particular questions or a particular approach to actually sift out what is fact and what is perhaps a story or an additional, you know, emotion that the team is attaching to that.
Yep, yep. I think the, the first thing I try to do is validate them so that they know this is a safe space to come and to present issues, to so validate that. That's a. I hear you, but then I follow up with some questions of, you know, I hear your issue. Do you have some specific examples? How many times has this happened? Do you. What client did this happen with? What individual? What was the impact financially? What was the impact to you, to your team? So ask those follow up questions. If they don't know the answers to that, maybe they haven't had this habit yet, then just say, you know, this is really important to me and I can hear that it's important to you. Why don't you go gather that information and then absolutely schedule a meeting with me or stop in my office, whatever your circumstances, and we will absolutely talk through this. If they do present you with some facts, then you still might have to sift through the information and ask some follow up questions. But I think that it's important to always ask those factual questions so that they know. Oftentimes we just need to vent a little bit because it emotionally doesn't feel good. But when we look at the facts, sometimes we can just work through it on our own. When it like, oh, this feels icky, but the numbers are not telling me that it is. So then they can start to decipher what the actual issue is the root, and then either on their own or with your support, they can come up with some potential solutions.
So it boils down from what I'm hearing to asking questions of specifically how many instances of a particular issue, specifically where, with whom, in what particular cases. So thanks for sharing more about, about that there. All right, put a pin on this for now. We can dig into that later a little bit more if possible. Now I would like to shift gears to another. And again, watchers and listeners, you really influenced this conversation because I didn't know if you would be getting into these points, but definitely quite a few people were curious about the tools and I am myself as well. For a role like yours, the coo, we mentioned ClickUp already and we can expand on kind of how you use it for your day to day. And not just that, but also, you know, we've got the quarterly sessions coming up. Right. And ClickUp plays a role there as well. What do you think are the most important tools in your job? Or maybe these are not tools in the sense of platforms or apps. Maybe it's something else. But I'm curious about the general answer to the question. What would you say?
Absolutely. And I will take a little liberty here and use the word tool loosely. Number one, we talked about organization, we talked about what tool works for me. I would say just find a tool that works great for you and for your organization. ClickUp or not. So that's, that's one. This is where I say I'm going to use this a little loosely. You need to take care of yourself. So you got to do the things, you got to drink the water, you got to eat the right food, you need to move your body, you need healthy sleep habits because you have to have the energy and the mental focus to, to do the job. So your team is depending on you to be sharp, make efficient decisions, make the best decisions. And so they really need the best of you. And so I would encourage you and you don't want to be exhausted at the end of the day. I hope everybody has a little bit of a life after work. And so you need the energy to have that. So, number one, take care of yourself. I would say ask for help. This might mean again, hire the right people so that you can trust them to do the work and you can let go of the vine and delegate some of the work. It might be a time where you need to ask for help. Maybe it's time for an executive assistant or some support in that area. Maybe it means it's in your personal life where you're going to ask for some meal prep service, some lawn care service, cleaning the house, whatever. It means, ask for help because you do not have to be. And I think sometimes at this position, oftentimes we get here not because we started out just knowing how to do this job. Oftentimes we start in one path of the organization. So you might lean into finance. Maybe you're more of an operations person, you know, maybe you're a salesperson and you grow and eventually take this path to this position. So that means you're probably not going to be an expert in every area of the organization. And that's okay. And so that's why you need to ask for help. I would say specific to tools, definitely be in a growth mindset. So I listen to audiobooks and I just pick. Because you can get through them fairly quickly, especially if you listen to them at a higher speed. I pick an area that I need to grow in. Maybe I've heard from my team that we're struggling in one area and so I'll listen to an audiobook that's in that specific area so that I'm always trying to grow in an area. And then of course, like I said, surround yourself with really great, talented people and that will definitely help. So that would be my tools.
That is such a cool answer. It's not what I was expecting. I was thinking, you know, you would be talking about maybe like 15, 5 and stuff. And I do want to drop some of these kind of a little bit later in the conversation. But it's so interesting how I was just thinking about it earlier today. I'll. I'll be honest with you with, you know, how important it is throughout the working day to just take care of your body, your brain. And I'm noticing a big difference when I'm more conscious of it. You know, this applies not just to leadership roles, although definitely not a well rested and kind of calm, mindful leader makes a huge difference because they affect whole teams of people and whole businesses. But even for myself on the days that I remember that I should probably not be pumping my brain full of dopamine from the moment I open my eyes, just take a breather. If I'm taking a break, if I take a break, and for once I don't scroll my smartphone, I just stare a little bit out the window and take a few breaths. It makes such a big difference. And in my day. And I also like the. I did the Gallup strengths test at some point, and one of my strengths was input. So what you were saying about audiobooks and having a growth mindset, I'm noticing that when I have enough good input and, you know, and growing in that direction, that really helps me day to day to be more inspired to have better ideas. So all of what you said really resonates with me. And on the issue of consultants, I feel like, you know, some. I hope there are some people listening to this right now and thinking, you know, my internal operations are a mess. Maybe not that necessarily, but they're thinking of, you know, there's some chaos, maybe miscommunication, maybe misunderstandings. And I would say, you know, there it's another way to put the burden off of your mind to just seek out somebody who's done this work. Chris dubois posted about this a few he's the host of the Agency Forward podcast. Shout out to him. He posted about this on LinkedIn a couple of days ago. The question he always asks himself is like, what are the winners doing? You can take a lot of burden off of yourself by asking that question. And hey, if your burden is related to ClickUp Project management agency operations zenpilot.com Colleen, you can talk with with us. So that was a lot of things to comment on. I have a couple of follow up questions and I think I finally understand your question, Adam, so I'm going to ask that in just a second. Well, you mentioned books. I got to ask what are some of your all time favorite books to fill your brain with good stuff and then anything you're listening to recently where you're kind of growing in that direction.
Yeah, I, this is just how my brain's wired that I really like anything that is a personal development book or I just, I struggle with fiction. It just, it's hard for me to stay focused on it because I, I need to know how is this going to apply to me right, right today. So if you love fiction, that's great. That's awesome. I will take your recommendations because there are times where I need to shut my brain off. I am just thinking, oh gosh. Because sometimes I'm listening to two or three at a time. The first one that just came to my, my mind and it was because of a prompt question that you had, is the book Radical Candor. I have. It's been a long time since I've read that book. I mean maybe a couple of years. But if you are somebody that maybe is struggling with those tough decisions or tough conversations, it's a great book because it really is talking about, you know, why people are worth having those, those difficult conversations and how to have those conversations. So that's just the first one that comes to the top of my mind.
But okay, yeah, good recommendation. I was looking in that direction because it is on my shelf right now. Yeah, my wife, my wife got it from her company for some sort of occasion a few years back. I haven't yet read it much, I have to say, but every time I have a conversation like this it puts one more point towards that being the next one that I read.
It's always great to have good, good recommendations about what to listen to next. I typically will listen to Audible, but check with your local library because our local library has an app and so I can download for free and listen to audiobooks that way. They don't have all of them, but I do that because it's, it's free. And then I lean into audible after that if I need to.
Yeah, yeah. And indeed it's not just audible. You mentioned fiction and I'm not going to talk about it for too, too long, but if you want to get into fiction, there's actually a lot of podcasts, good podcasts on like Spotify, Apple podcasts that are a little bit easier to digest because it's not like prose in audio form. It's a little bit more episodic. Often it's just easier to follow. And I'm going to drop my favorite like it's September. Spook season is upon us. My favorite horror podcast is the Magnus archives. Now continue with the Magnus protocol. If anybody wants to listen to something good, that's that. So I recommend that. Now I have a follow up question about actual tools that you use, but also on the subject of great talented people, we have a question coming in from Adam here. So I'll read the question. But I also read, kind of also give you my interpretation of the question, almost kind of covered by the, by the box here. And with the two combined, I think we can give Adam a good answer. So he's asking, is there sometimes a leading indicator that says, no, we aren't hitting a workload limit. Let's find a way to make this more efficient. How do you find this stuff? If you're an ops leader responsible for people who might know how to do things that the ops leader can't do themselves because they have other skills. The way I understand this question is let's say you have a team of copywriters and they're saying the blogs or this copy, it takes as long as it takes. This is the amount of hours that's needed for this particular type of work and you have either a feeling or you're given some external input of this type of work should not be taking this long. There's still more efficiency to be found. So the question is about an indicator, maybe a way to run this conversation of is the team being as efficient as they think they, they could be, is there more efficiency to be found here? Long winded way to ask. But what's the answer?
I don't know that I have a scientific answer other than more investigating, because that does happen. And so they'll say, and if you don't have, you know, really hard evidence or data, you're going to have to ask some questions or you might have to do some poking around on your own or some inquiring and. Or you might have to go look back a year prior or two years prior and look at what, what did it look like? You know, let's say we had four copywriters, but we had. The workload was much more. And so sometimes you just have to take some best guess or do some investigating. And it's really hard because you're going to be asked to make a decision that's concrete based on maybe not concrete evidence. Sometimes we make the right decision and sometimes we don't make the right decision. So I know that's not a great answer, but I would say investigate as much as you possibly can, poke around and compare data and see if you can just make the best decision with what you got.
I like that answer. I feel like a part of this as well. That comes to my mind at least, is a part of the answer here might be networking, actually talking with your peers, you know, with a similar team, you know, do they also find that this type of work takes X amount of time, you know, getting some perspective, but it's part of what you're saying, investigating?
Absolutely. I have done this a number of times with colleagues that are not associated with our organization, where I'll call and I'll say, is this, Is this how this financial reporting structure should look? Is this how, you know, our book should look? Is this what. How many hours does it take your copywriters to do this? So absolutely. Ask trusted sources, though. I would say that.
Yeah. And the last thing I'll add on top of that, Adam, in terms of indicators, again, within ClickUp as a system, there's ways to quantify that in a more concrete way. There's time estimated, time tracked, and with good time tracking practices in there, that becomes easier. And again, there's an episode of Agency Journey for that you can look up zenpilot Time Tracking. You'll find Best ClickUp time tracking practices. We have a video on that and I have a podcast with Gray all about time tracking. It's called the 40 hour conundrum. So that's about kind of how to approach it from a leader's perspective, just in case anybody wants more content. Because as I mentioned, we only have this one small hour here. We've only got 20 minutes of it left, which is so tough. Okay, so watchers and listeners, if you have more questions, definitely drop them in the comments section because we are limited on time here. My next question was going to be Sean, we talked about, I mean, asked you about tools. You gave a fantastic answer of like taking care of yourself, getting inspired, surrounding yourself with talented people. But I would love to know also about particular tools, platforms, apps, you know, an app on your phone that you can't live without or maybe something on your computer. Computer. What would you recommend as like essential tools in your toolbox?
Well, I can't live without my calendar. That's just. I feel like my entire life revolves around my, my calendar. Even our family is programmed that way where everybody's, everybody's got their own color, their own thing. So that's, that's the number one thing I can't live without. But you know, I love HubSpot. Salesforce is great too. So if you need to, you know, track your leads, track your, all of your sales. Love that I have used. Of course we're, we run on Eos. I love Eos and we've used. We're fortunate because, you know, we, because of ClickUp, we use all of Eos is in there. But I've used 90 in the past. For anybody that is running on Eos, I absolutely love 90. It's really robust. Let's see, for people and culture tools, we use 15 5. There's a free version of it. If you don't want to pay for all of the, the seats I have used. Let's see. Oh, Gusto. If you're in the operations people space and you need to do payroll or you're in that space. Love Gusto. I think that's a great tool. There's a lot of tools that we have that I would say look for what the free version is and see if you can start with the free version before you start to pay money. One of the. And I've been in an organization where this has happened where there we had so much SaaS expense because if an issue was presented, it was solved by purchasing SaaS. I don't like that because now you've got the team using too many tools. Their attention is spread everywhere. I would rather see if you could use less tools that are more efficient or start with the free version before you move to the paid version. Of course the paid is going to have all of the, the tool, the features and benefits that you want. But see if it works for you on the free before you invest money in it because one of your, your jobs is going to be to make sure that you're profitable. So if you can save on some of those Expenses and not just save money, but save mental space by using less tools. I actually would recommend that.
I'm curious about the calendar piece of it. Do you use a particular app or just regular Google Calendar? Something else.
I use Google Calendar and I mean I have. This is more personal life. I have a calendar that shows is my meal planning and it's shared with my kids because they used to always come home and say what's for dinner? And I just, it was just too much in my brain and so I put it on a calendar and I shared it with them so they could see stop asking what was for dinner or if they would come home. And I have no college and high school age children but they would come home and they would say I need XYZ for, you know, I need a new thing for tomorrow. I need a new hockey stick and I need it tomorrow. I would try to teach them. And you do this with your team too. Put it on the list. Just put it on the list. So that when I'm ready to mentally deal with it. So again you create efficiencies in your personal life and your professional. Professional life. So when you're ready to tackle your list, it's all right there.
Yeah. Yeah. I love that. And wow. Meals on the calendar. I. I am curious about that. That is a huge tip for me.
For me personally, the other calendar tip I would have is you can and there's lots of different templates out there for what an ideal work week would look like. You can overlay so you can create a calendar and create blocks for what your ideal work week looks like and you can overlay it over your existing calendar and you can see where you've got some issues that maybe you need to start moving your meetings around so that it's your energy, it matches your energy level. So I try and batch my work so you know, maybe Mondays and Tuesdays are heavier meeting days that maybe there's a little bit more information administrative on the back end of the. It's just where my energy lies. So you can easily do that to see where you could make improvements in your own schedule.
Yeah, respecting your rhythm is huge. I think this is something that partially you said and partially you discover you always have an ideal in your mind and then you realize I can't write for eight hours on a single day. You know, I can do research for four and then writing for three. And I do need to also take some sort of break and move my body somewhere in there. These are of course made up numbers, but that was A recent epiphany for me as well. And I asked myself at the beginning of the day, where do I need to apply? What's the most complicated problem to solve? And for me, actually I decided to spend the first chunk of my day on home management stuff. Plan out the week, think about the meals, think about the groceries, because for my brain that's the most tough. And then when I get into the marketing stuff, it almost becomes easier. So anyway, on the subject of tools, some others that we use that I would recommend, and they're almost kind of invisible, but you mentioned you can have a few SaaS subscriptions, you can have more. But one thing that ties it all together for us is one password. I mean a password manager for the team. Super useful, makes onboarding easier. I even remember my onboarding ads and pilot. I just got access to one password and everything is in there. And we use textexpander, which is a huge efficiency boost. Textexpander is cool because it's a text shortener that expands into links, expands into pre prepared chunks of text. But also you can store these and update these company wide. So for example, Gray moved some time ago to Mars, Pennsylvania. So the company kind of official address changed, but the shorthand for it didn't change. So it just changed output something different when, when somebody wanted to leave their, their company address. So I just thought I would add those two in there.
Yeah, it's great. We, of course QuickBooks, if you're a smaller organization, you, most companies will run their finances through that until they, you know, are large enough that they need their own. So I'm in QuickBooks every day. I absolutely love that.
Yeah, yeah. Okay. Awesome. Awesome. Alrighty. So, and we could talk really about tools all day long, but to finish things off. And again this is thanks to the engaged watchers and listeners today. I was curious if there would be interest in the EOS piece of it all because not everybody knows EOs, not everybody is on the US but at least a couple people expressed interest in the point that we had, which was succeeding as an integrator. So let's look through the EOS lens for a second here. Definitely. Let's start with a brief explanation of what it is for those that aren't familiar. And then what is an integrator? How is that role defined and how do you succeed in it from your perspective, Sean?
Yeah, exactly. So EOS stands for Entrepreneurial Operating System. And there's a book I would recommend people listening to or reading the book Traction. The abbreviated version is called what the heck is eos? It's truly a way that you can structure your organization to get things done. I mean that's, that's the simplest way that I can define it. EOS has, I'm sure, a different way of defining it. The integrator role is on the accountability chart. So if you think of an organizational chart, EOS calls it an accountability chart. And it's because you truly want each person to own an aspect of the business so that it's crystal clear who does what. The visionary and the integrator are counterparts and oftentimes the owner, your CEO is going to be the visionary and then the integrator is truly going to be the. I'm going to implement all of those ideas, I'm going to get those things done and I'm going to get them done in a way that creates the least amount of chaos for the team and moves the company forward in the best direction. They're, they're almost the, the opposite. The way you can tell if you're an integrator, there's a free assessment tool, it's Rocket Fuel or you can go to EOS and look at rocket fuel. And that really is, there's a book specifically called Rocket Fuel and that is going to tell you it's an assessment and it's going to tell you on a scale where you fall if you're an integrator, a visionary, or maybe neither of those. And so that is how you're wired then. The other piece that I would suggest is there's lots of EOS tools out there, whether it be the website, Facebook groups, there's a couple different ways you can implement EOS into your organization. I've been with organizations that use an implementer to help roll that out to your organization. And then there's an organization that I was with where they self implemented and so they did it theirself. I would say as an integrator, if you're interested in it, take the assessment number one, start to join the community and find like minded people, see if it's a good fit for you and then you can start to possibly look for either organizations that have done it or you can present that to maybe your CEO or the owner and see if that's something that they would be interested in. I would say to be a successful integrator, the key is, well, there's a few keys, but I would say that relationship between the visionary and integrator, it takes a lot of respect for one another to understand that you're, you're wired completely different and how you do things is completely different. But that's the magic, because when you work together, you'll get way more done. You know what, what is it? The two strands woven together are stronger than just the two separate strands phrases. But so understanding and really, truly respecting each other and how you work is really important. And then as that integrator, you're truly, you sometimes have to make those tough decisions. Sometimes you're the tiebreaker. And so you have to really decipher what idea we're going to take and run with and in what order so that you get the most amount done. So it's kind of a broad overview of the integrator role.
I love that. I love that. And I'm so glad I asked. So there's one thing you mentioned, particularly on one of our meetings recently that I was curious about and I would love for you to talk about a little bit. So I saw on your calendar and Gray's, Gray is the visionary, you're the integrator. These same page meetings and whether within EOS or within co founder, co founder relationship, can you talk a little bit about like what these meetings are for, what they entail?
Yeah, absolutely. I would encourage anybody, whether you're an EOS organization or not, to definitely have, whether you call it a one on one meeting or a check in meeting and find the cadence that works best for you. And so Gray and I do have that. We've got one on one meetings and oftentimes they become about here's, here's the issue, here's how we solve it. Almost like a to do list. These are, this is how we get things done and we cross things off a list and we follow up with each other. Oftentimes we can do them async, but we do have those meetings and we have them weekly in a remote environment. I think that's nice to have. In addition to that, we have what's called a same page. Again, that's an EOS term. You know, if you're not eos, you can take the same concept and run with it. A same page meeting is much more than just are we getting the things done or what are the answers to these questions? This is truly, are we on the same page? So are we actually adhering to our vision and our strategic plan and am I aligned with that? Do I know what the goal is for the next five years? Are we headed in the same direction or am I, did I understand his vision correctly? So he might have ideas that are generated oftentimes visionaries will have constant ideas. They're flowing, they're coming from every direction, and they're not always chronological or they're not linear. They're kind of all over the place. And so the integrator's job is to kind of bring those all together, organize them in a nice neat way. But that doesn't mean that I'm going to interpret the vision his way or correctly. And so it's good to have that time to say, am I understanding this correctly? Did I hear you correctly? Or for him to say, that is not at all the direction I was going that I was thinking we were going to take, but also taking the rest of the team, I need to be able to say, well, here's why. Here's why this is not working. You know, I know this was your idea. That's great. But our staff or the clients are not responding to it, and here's why. So I think it's important to have those. And I think we sometimes struggle to slow down and work on the business that way. We want to get things done, but I think it's really important that we actually step away and have those deeper conversations. Communication is key, right?
Yeah, I love that. And a part of this that you illuminated for me is that it's not just that the visionary has the vision and you're making sure that you understand it regularly. It's also you helping keep the vision maybe not so much a moving target, because it's true that the vision can change over time. But I feel like part of this is also saying, okay, so, you know, last time we met, you were describing this in this certain way. Now it's a little bit different. So what are we ultimately deciding on? Bringing it a little bit more down to earth and making it a little bit more concrete.
If I understood you're correct, it's 100%. And that is typical of a visionary and an integrator, where the integrator wants to see. The one complaint visionaries will often have about integrators is that they're moving too slow and it's not necessary or they're not getting enough done. But in reality, it's that they're trying to do it in a systematic way to reduce the chaos. And of course the integrator is going to say that about the visionary is, you had an idea yesterday, and now we've got a different idea today. And. And so if they have a lot of respect for each other, it's powerful. It can get a lot done.
Okay, awesome. Awesome. And oh gosh, we're almost out of time for, for this session today. I feel like this was packed. I'm gonna do, what I'm gonna do is I'm gonna pull up the slides back up and show some things here that our watches and listeners can make use of. In the meantime, I wanted to just ask you the insurance question, Sean, and the insurance question is, of course, is there anything else that you wanted to mention in this topic as part of the COO survival guide that I sadly neglected to ask about that you would like to add in as the final piece?
I don't think so. I don't think so. Yeah, we tackled a lot in a short period of time.
Yeah, I'm very happy about that and I hope you are too. Watchers and listeners so just a few last things that you can get from us at zenpilot. We mentioned ClickUp quite a few times here. If you're curious about ClickUp, if you're on ClickUp or you just want to do better in tracking your work keeping everything in one system, I recommend that you go to zenpilot.com resources. We have free ebooks, we have video guides, we have ClickUp templates that you can plug and play. So you can see how we organize things in ClickUp following what is called the Zen Pilot system because we're opinionated about how to set things up in ClickUp in the optimal way, using the most of its strengths and avoiding the most of its weaknesses. As a reminder, if you want more events like this to hear more from me, from Sean, let's have you on another one of these. I think this one was, was really cool. More from Jeff, our productivity professor and our CEO Gray, and some other pilots besides. Definitely sign up for our newsletters and pilot.com newsletter. And last but not least, if you're dealing with chaotic operations, if you would like to have if you would like to see what is the best way to set up, click up the I like to call the optimal way. Gray always gives me pain about it. You know, optimal may not be the right word, but a battle tested way of setting up ClickUp and setting up your operations in general for increased accountability, productivity, efficiency, profitability. Then get a call with our team zenpilot.com call it's like think of it like free project management ops therapy. Tell us about your issues. We'll point you in the best direction. Whether that's working with us, whether it's making use of some of our products or maybe something else entirely. It's always worth meeting our team and it will be an inspiring conversation, I assure you. And that's it for today. I wanted to thank first of all the watches and listeners for coming here today and joining us and leaving comments and steering the conversation, giving us a little bit of insight on what to talk about. And you, Sean, did beautifully. Thank you so much for agreeing to this the first time I'm having you on the Zen Pilot live show and you did so great. Thank you for agreeing to come on the show.
Thank you, thank you. It was really fun to be here with you and spend some time with you and hopefully, hopefully the listeners got at least one nugget out of it.
Yeah, I think they definitely did. More than one. I learned myself a lot, particularly in the Tools section. I can't wait to share the replay of this in our newsletter and maybe on our blog as well. But anyway, for today, unfortunately, watchers and listeners, this is all so thank you so, so, so much for joining us here today. And that's all folks and we'll see you next time. Thanks everyone. Have a nice rest of the day. I'm going to hit the end stream button now. Bye bye.










